Jrue Holiday’s debut season with the Boston Celtics has been smooth sailing, however, the 33-year-old still needs to find middle ground with the front office to remain with the team for the coming years.

With Jaylen Brown, Kristaps Porzingis and Payton Pritchard signed to extensions ahead of the regular season, Holiday’s impending contract dilemma has yet to be addressed. The Celtics surrendered Robert Williams III and Malcolm Brogdon to acquire Holiday from the Portland Trail Blazers, allowing the three-time NBA Teammate of the Year the chance to contribute again to a title contender — which Holiday has.

That still begs the question: what’s next for Holiday and the Celtics?

“I think you need to see how things look in the playoffs,” an anonymous Eastern Conference executive told Heavy.com’s Sean Deveney. “It’s risky because if they roll through to the Finals and win that easily, you’re under pressure to give him a big contract. But at the same time, you give Jrue Holiday a big deal now, and they flame out in the playoffs, lose in the second round, then where are you?”

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Holiday isn’t the No. 1 or No. 2 scoring option for Boston. But… considering Holiday was the defensive captain in the 2021 NBA Finals for the Milwaukee Bucks, and has assumed said duties alongside Derrick White with the Celtics, expectations will still be high. That won’t change.

So far, reports have indicated mutual interest between Holiday and the Celtics, but the contract numbers could get complicated. Holiday’s eligibility grants him the chance at earning $51 million in annual salary, which of course, could derail the current core Celtics president of basketball operations Brad Stevens worked to create in the offseason. Since Holiday’s entering his age-34 season in 2024-25, it wouldn’t make sense for Boston, or any team across the league, to cough up that kind of dough.

“I think he is going to want $100 million, you have to pay for what you’re getting,” the executive continued, per Deveney. “He’s giving you all this leadership, the defense, all these little things that make you win. The tax bills are going to hurt. But that could be where this all winds up.”

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Holiday’s been at the forefront of re-establishing Boston’s defensive identity while providing an offense-stabilizing approach that’s helped limit costly miscues. He’s averaged 12.6 points on just 10 shots per game and leads all East point guards with 5.5 rebounds and shoots 48.1% from the field. When it comes to shooting the corner three, Holiday’s also been the best, leading the NBA, draining over 60% from the left and right corner.

The hunt for Banner 18 is the primary concern for everyone in Boston’s locker room. That’s evident in the team’s league-leading 62 victories, long-lasting No. 1 seed (since Nov. 14) and overall sacrifice-promoting mindset.

Holiday has a $37.3 million player option remaining, which the Celtics could settle through a multi-year extension.

Featured image via Bob DeChiara/USA TODAY Sports Images